(2-Fluoro-5-propoxyphenyl)boronic acid → HCID 59226511, compound

HRID 1523479Notes

Reaction equation

HRID 1523479 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][C:5](Br)=[C:6]([F:8])[CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]=1B(O)O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][C:5]([C:19]2[CH:18]=[C:17]([O:20][CH2:21][CH2:22][CH3:23])[CH:16]=[CH:15][C:14]=2[F:13])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 16217464(2-Fluoro-5-propoxyphenyl)boronic acidHCID 726988793-Amino-6-bromo-5-fluoropicolinic acid

Product 1

HCID 59226511HCID 59226511, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 178418807HCID 178418807, compoundCatalyst

Procedure

Method 1 was followed using 3-amino-6-bromo-5-fluoropicolinic acid (1.0 equiv.) and 2-fluoro-5-propoxyphenylboronic acid (1.3 equiv.) and Pd(dppf)Cl2-DCM (0.05 equiv.) to give 3-amino-5-fluoro-6-(2-fluoro-5-propoxyphenyl)picolinic acid in 28% yield. LC/MS=309.1 (M+H), Rt=1.00 min.

Sources & evidence

ORD record
ord-9c00bfb5d136411b93cf8ec05da8d276
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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